Welcome To Hell
by NotAShipAnArmada
Summary: Demon!Dean and reader insert. You are in a female format if you are reading this. Very NSFW


"I swear Tracy, if this new trailer for Fifty Shades of Grey was any worse, I might just cry. It is so ridiculous and demeaning. Real BDSM scenes wouldn't be anything close to that." You say to your long time friend who nods, staring down into the slightly cloudy drink she calls a dirty cosmopolitan. Taking a sip of your own drink, a more regular pina colada, you glance around with a sigh.

"Writers don't do any research anymore, you know that. They get the basic facts then say screw it and bullshit the rest." Stacy replies and lets out a little giggle, blue eyes sparkling with delight. "And I think we just caught the attention of someone with our conversation…" She murmurs, blood red lips quirking up in amusement. You turn around to look at one of the booths her gaze is caught on only a little ways across the smoky bar. You catch a flash of emerald green eyes, sandy blonde hair and freckles before turning back around, cheeks flushing gently.

"Probably just curious about the way your cleavage is hanging out of that ridiculous top." You tease and she laughs, shaking her head.

"Sure, whatever. You and your prim and proper little white blouse and pencil skirt. Honestly, you never have any fun." You frown a bit at her, despite the obvious jest. You had fun… Just not lately. Being focused on your job was more important after all. Stacy sighs and gets up with her drink.

"Well, I'm going to see if I can nab another drink from the cute bartender. Maybe you can make doe eyes for a bit at freckles. He's still watching you." You can feel your cheeks flush more heavily at that and you glare at her as she bounces across the deep red carpet, skirt bouncing with the movements. Maybe she was right; maybe you did need to have more fun… Just as you were contemplating possibly going up with her, you are startled out of your thoughts when someone lays their hands on your shoulders.

"You know," Drawls an obvious southern accent, as deep and smoky as the bar. "BDSM is not something to play around with lightly. Especially for someone of your… Nature." The voice says with a little snicker before the hands are gone and the stranger with the green eyes is sitting across from you. A million thoughts race through your mind before settling on one: _Why did Stacy have to leave?_

"What do you know about my nature? You've just been staring at me and listening in on our conversations like some creep." You say, trying not to let your voice waver. You were so confident usually, but there was something about him that just sent a shiver up your spine. A delicious one at that, something that made your lips tremble, and a delightful curl of danger swirl in your stomach. The man laughs and leans back in the chair, cocky in the way he relaxes, hands resting easily on his thighs as he tips the chair back a bit on its legs.

"A creep huh? Oh darling, you have no idea. Though you are wrong in the way you think I'm creepy, possibly even frightening." His grin is practically maniacal but you find yourself drawn in anyways, despite your mind yelling at you to run and get away right now!

"And what way should are you creepy then? A way that should keep me on my toes I assume?" You ask almost breathlessly, entranced slightly by the swirling of green and gold in his eyes… That is until they gloss over midnight black and you jump a little, heartbeat thrumming and your head screaming _Not natural! Wrong, so very wrong, run!_

"Perhaps this gives you an idea? Of the danger you are toying with?" He purrs and your warning thoughts skid to a stop as you shudder, his voice like oil sliding over your skin but in the best of ways. This was wrong, but yet…. Wasn't this what Tracy wanted? It couldn't hurt to simply test the waters…

"I'm not toying with anything. I'm simply trying to figure out what your purpose is to coming over to me? If you are so dangerous, I don't see why you would be interested in me. Apart from the conversation you overheard…"

"And that right there is why I'm here. You don't think that book, however pathetic it was, met the real standards of life and a world I doubt you even know much about." You bristle slightly at that, how dare he even assume you hadn't done research?! Before you can say anything though he reaches across and drags a finger down your neck and slowly across your pulse point, feeling it jump as your heart stutters again and you swallow deeply.

"What do you think of a dangerous situation with a dangerous stranger, taking you to new highs and lows within minutes? Showing you the definition of a pleasurable pain that borders on too high of sensation? Of someone possibly doing things so out of your comfort zone it makes you squirm, makes you _writhe." _He almost snarls the last part, making your body twitch and you realize your breathing has picked up, eyes half lidded as you listen and focus on the feeling of his fingers toying with the lace on your high collared blouse.

It takes you a second to realize that suddenly those fingers are gone and he isn't in the chair anymore, and only another beat of confusion before he is behind you, hands wrapped gently but still firmly around your throat right under your jaw and you gasp.

"How do you feel," He whispers lowly in your ear, his free hand curling around to touch your waist through the loosely hanging fabric, feeling your muscles tremble lightly. "About someone not letting you have a say, gagging you and taking what they want?" He ends that with lightly running his tongue along the more pronounced vein beneath the skin of your neck, making you gasp and squirming, digging your nails into your thigh. "Answer me!" He hisses, fingers tightening on your throat and making you whimper and clench your thighs together.

"Yes! Yes, I want that, It sounds amazing and perfect!" You gasp, almost shocking yourself with the way you jump at his command. You had never done that before, you were always against people ordering you around, but here you were… Obeying. After a moment he chuckles darkly and takes a step back before offering you his hand, which you take almost numbly and stand, letting him turn you to face him. Even in heels, he still towers over you by about five, maybe six inches. It's exhilarating, combined with what he already did and said.

"I-if we are leaving I have to tell my friend." You stutter out and he laughs, shaking his head as he tugs you close.

"No need darling. She left with the bartender ten minutes ago. You're all mine tonight." He smirks and that leaves you reeling a bit. Ten minutes? Had that much time passed in such a small bit of conversation? Silently, you nod before letting out a shocked bubble of a scream as you are jolted and are suddenly falling back on a plush grey comforter on a very large bed in a very large, darkly adorned room. The man, you still haven't gotten his name, is simply grinning down at you, arms crossed over his chest as his eyes roam over your body.

"Wh-what are you? That wasn't- You just…" You stammer, looking everywhere but those endless black eyes of his. When had they switched back to that?

"Perhaps we should simply stay with danger incarnate? No need to complicate things further. " You simply nod, lips parted a little as you watch him strip off the black button down shirt he had been wearing, a little dumbstruck by the muscles he was hiding.

"S-so… Um, what is your name? You never told me…" You manage to get out, cheeks flushed as you avert your eyes as he drops his pants but leaves his boxers. For now.

"Names are frivolous to me. But if you must, it's Dean. Now stand. I want you to strip for me. And as you do, think of a safe word, though I doubt it will do you much good." He laughs again and the darkness of it makes you shudder again, even as you scramble to stand, wobbling a bit in your heels before kicking them off and starting to hurriedly tug out your blouse from your skirt.

"Stop." He says, simply but the sharpness of his tone makes you stop dead, wide eyes flicking to stare at him, waiting. "More slowly, we don't want to rush things now, do we?" He smirks and you shake your head quickly, a few stray hairs pulling away from your tight bun to frame your face. He leans back on his arms as you slowly unbutton your blouse, his hungry gaze boosting your confidence slightly so you reach back once all the buttons are undone to tug out the pin holding your bun in so your hair drops in waves along your shoulders. Somehow it seems like his black eyes darken and you slowly shrug the blouse off, biting your lip as you wriggle out of your skirt. Before you can do anymore, he stops you with a hand up before curling his fingers in a come here motion.

You walk over, nervously standing before him as he sits up and places his hands on your waist. You close your eyes, reveling in the gentle sensations of him running his hands upwards before gasping as he practically rips the hooks on your bras, the article coming off so easily that you wonder if you weren't imaging the ripping of seams. The sudden motion sets you on edge again, itching to cover yourself as he leans in to mouth at your stomach, just under your breasts and making goosebumps erupt all over your body and a little moan to leave your lips. This wasn't so bad after all, you start to think before jerking in his grasp as he suddenly bites down, not hard but sharp enough to feel a burst of pain and you whimper, hands clenching his shoulders almost hard enough to draw blood.

"Dean, that… That really hurt…" You whisper and he simply laughs before standing, walking around you and carelessly shoving you face first onto the bed. You bounce slightly and give a sharp little hey! Before he grabs your wrists and wrenches them up towards the top of the bed, dragging your body up slightly with the motion and squirming at how tense it makes your muscles. You try to look behind you to see him, but before you can there is the snick of a clasp and there is metal digging into your wrists, not uncomfortably but not loose enough to completely relax into the set of cuffs you hadn't noticed on the headboard.

"That is what you get for talking without permission." He growls and you tense under his gaze, his hands no longer on your body. The room goes silent and you know he is still there but all you can feel is his gaze and a slight dip to the bed behind you between your legs…

CRACK! It takes a millisecond for your brain to register the sharp, startling pain of the spank, body lurching and a sharp cry leaving your lips as tears spring to your eyes with the surprise.

"For every sound you make, I'm adding another five. You are starting at five. Now, what is that safeword I asked for? You can speak this once." He says lowly, hand rubbing gently over the throbbing, red part of your bottom and making you whimper.

"U-um… Lollipop I guess?" You whisper, afraid speaking too loudly will bring about more of the harsh spanks, but a part of you almost wants to be snarky, to tell him off… "That is sweet enough, unlike you." You hear yourself say and there it comes, the lightening bolt of pain from before, this time on the other cheek and you let out a loud cry before remembering you need to be quiet and biting your lip almost hard enough to bleed.

"Don't be snarky, bitch. Just for that, and the cry, you are up to twenty." Another slap comes down and you push your face into the pillow beneath you, trying not to moan even as you body jerks and you almost push back. You were shocked by your reactions, but the pleasure coming from the pain was so shocking you couldn't focus on anything else anymore.

"Now stay quiet for me, otherwise I'll have to think up another punishment for you." You can hear the sneer in his voice as he starts to really lay into you, and it becomes harder and hard to not cry out or moan, tears of frustration gathering in your eyes as you grit your teeth. Finally, he stops and you can feel the bed dip as he climbs off again.

"Roll over for me darling." He coos, and the gentle tone throws your mind for a loop, in contrast to the spanking you just had. Trying not to whimper too much, you grasp the cuff chains and roll over, wrists now crossed as you lay exposed on the bed, watching Dean as he watches you.

"Did you like that, naughty girl? You aren't supposed to like your punishments." He says in that scarily calm, nice voice as he walks back to the end of the bed and spreads your legs completely apart. The position makes your cheeks flush a deep red but you can't be a bit eager as you arch your back, trying to make yourself look more desirable. It seems to work, as you manage a low little growl out of Dean and he is suddenly looming over you, one hand on your chest between your breasts and pushing you back down.

"Someones eager, hmm? I shouldn't reward you for that, but you are a newbie…" He murmurs, leaning in to suck a mark into your neck before biting down sharply just as he moves his hand sideways and pinches your nipple, making you gasp and arch right into his body. When he pulls back again you practically sob, body aching to be touched.

"Dean, please…" You whisper, trying not to beg but damnit you need to be touched! He simply gives you an amused look before running a hand down your stomach, feeling the muscles quiver and laughing when you whimper as he drags a finger along the seam of your thong.

"Perhaps I can give you a little break." He murmurs before slowly pealing your panties off, exposing you to the cool room. This time you don't hesitate to spread your legs for him, panting slightly with expectation of something, anything. What you don't expect is the sudden intrusion of two of his long, and thick fingers entering you sharply, your body jerking and a loud moan being wrenched from your lips, especially as he starts up an almost brutal pace, ramming his fingers into you and practically jabbing your sweet spot, making you cry and jerk on the bed.

"I don't think you really deserve me yet." He muses, despite not stopping or letting up on his brutal, agonizingly perfect pace. You can barely even comprehend what he is saying, despite trying as hard as you can.

"Please, Dean, please! I need you! I can't- I can't handle it!" You beg, body clenching with the need to climax, but unable to, not yet. You need more stimulation. Suddenly, there is nothing and you let out a miserable whine, hips arching off the bed slightly.

"Ah, ah, ah, not yet there sweetheart. I don't think you are quite ready… But I know an easy way to fix that." You slump back on the bed with a whimper, trying to rotate your neck to an angle where you can see what he is doing. It's hard though and you fall back to your original position. Finally, he moves back into your sight range, but not for long. He leans in and places a silk blindfold over your eyes, making you frown slightly and squirm as he pulls the elastic back over your hair. The darkness sets you more on edge and you strain to hear where he is. There's nothing, then he's pushing at your legs again and you part eagerly, hoping you are going to finally get him…

Something hard and more solid enters you in a swift slide, your body slick with arousal enough that it makes it easy. When the toy bottoms out you let out a pleased sigh, though it really isn't enough.

"… Dean? What are you doing?" You ask nervously, clenching around the hard length of the toy. It doesn't feel special at all, just a basic dildo of sorts, straight and-

"Oh! Dean!" You cry out, sudden harsh vibrations jolting through your body and making you arch off the bed, toes curling as your eyes roll back a bit. You hear him chuckle, despite the pleasure suddenly running through your body.

"Now, I wonder how long you can last like this?" He says from way too far away for you at that particular moment, until you hear a door open and close, only the vibrations and your harsh panting filling the room.

"Dean?" You whisper, biting your lip as you try and get past the vibrations and listen for him. "Dean? Don't you dare leave me like this! Don't you-" The vibrations go up another notch and you practically scream in frustration and pleasure as you try and grind down against the toy, much to your avail. You aren't sure how long goes by with you like this, the vibrations slowly getting more and more intense and your body sezing each time he adjusts the dial from somewhere you don't know. Finally, after what feels like hours you hear the door open again and you practically sob in relief.

"Oh Dean, please! Please, I need you so badly! I can't handle it, I need to cum, please, please! Don't leave me like this any longer!" You are practically sobbing now, tears dripping from your eyes and being soaked up by the blindfold. As suddenly as they started, the vibrations stop and you slump down on the bed, panting and body twitching from being over sensitized, especially when he slowly slides the toy out of your body, making you whimper and jerk.

"Such a good girl." He murmurs, kneeling between your legs and running his hands up and down your sides gently as you arch into the touch despite yourself. "You took it so well, didn't you? Do you think you deserve a real reward now?" You nod before you can think it over, desperate to please after knowing you hadn't pleased him before.

"Please, please… I want to be good for you…" You whisper, pushing your hips up slightly. You hear him chuckle again but he moves closer, grasping your legs and pulling them up slightly, setting your forelegs on his shoulders. The blindfold is suddenly removed and you blink up at him, wondering how you look to create such a look of animalistic hunger on his face. You can't think on it long though, because just as suddenly with the vibrations, he's leaning down and pushing into you sharply, making you gasp as you suddenly try to adjust to his wide girth.

"Oh God, Dean! Yes, please, take me!" You groan, throwing your head back as you flex your fingers against the chains on the handcuffs. He sets up a fairly brutal pace right off the bat, teeth bared slightly as he leans up, grabbing your legs and holding them up and apart as he fucks into your body, pulling cries and moans from your lips as easily as he got you to submit to him.

"Don't you dare fucking say his name." He growls and thrusts harder, deeper into you in punishment and you cry out, almost scream.

"I promise! I won't, oh Dean, Please! Yes, Ah!" You feel your body tense in preparation before letting out one final, desperate scream as you dive headfirst into your climax, jerking against the handcuffs and clenching tight around Dean who actually groans and thrusts just that bit harder before stopping, body shuddering slightly as he moans, black eyes seemingly focused upwards as he climaxes deep inside you.

After a moment he pulls out of your body, making you twitch from the sensations and slight soreness. He gets up and pulls on his boxers before unlocking your handcuffs and retreating to the bathroom. He comes back with a cool washcloth, and you barely react to him rolling you over and rubbing over the sore, red handprints on your ass, a throbbing reminder of your night together.

You're just about to fall unconscious when he crawls back into the bed and pulls you in close, brushing a strand of hair off your neck before kissing the deep bruise there and whispering, "Even a demon needs affection sometimes." That is the last thing you remember before waking again to screams and a grinning Dean.

"Morning Darling. Welcome to Hell."


End file.
